DE165562C - - Google Patents
Info
- Publication number
- DE165562C DE165562C DE1903165562D DE165562DA DE165562C DE 165562 C DE165562 C DE 165562C DE 1903165562 D DE1903165562 D DE 1903165562D DE 165562D A DE165562D A DE 165562DA DE 165562 C DE165562 C DE 165562C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- cyanoacetic ester
- sodium
- guanidine
- ureas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 235000013877 carbamide Nutrition 0.000 claims description 8
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- -1 cyclic ureas Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGRPCPCQQPZLZ-UHFFFAOYSA-N n-carbamoyl-2-cyanoacetamide Chemical compound NC(=O)NC(=O)CC#N QJGRPCPCQQPZLZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT27422D AT27422B (de) | 1903-11-14 | 1905-11-04 | Verfahren zur Herstellung zyklischer Harnstoffe (Pyrimidine). |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE165561T | 1903-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE165562C true DE165562C (en:Method) |
Family
ID=43432248
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1903165561D Expired DE165561C (en:Method) | 1903-11-12 | 1903-11-12 | |
| DE1903165562D Expired - Lifetime DE165562C (en:Method) | 1903-11-12 | 1903-11-14 | |
| DE1904170657D Expired - Lifetime DE170657C (en:Method) | 1903-11-12 | 1904-01-28 | |
| DE1904170555D Expired - Lifetime DE170555C (en:Method) | 1903-11-12 | 1904-01-28 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1903165561D Expired DE165561C (en:Method) | 1903-11-12 | 1903-11-12 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1904170657D Expired - Lifetime DE170657C (en:Method) | 1903-11-12 | 1904-01-28 | |
| DE1904170555D Expired - Lifetime DE170555C (en:Method) | 1903-11-12 | 1904-01-28 |
Country Status (2)
| Country | Link |
|---|---|
| DE (4) | DE165561C (en:Method) |
| FR (4) | FR349353A (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE752285C (de) * | 1942-04-29 | 1953-07-13 | Henning Laokoon Chem Pharm Wer | Verfahren zur Herstellung von 1, 3-Dimethyl-4-imino-2, 6-dioxohexahydropyrimidin |
| DE1130812B (de) * | 1960-06-24 | 1962-06-07 | Dresden Arzneimittel | Verfahren zur Herstellung von 4-Aminouracilderivaten |
-
0
- FR FR4153A patent/FR4153E/fr not_active Expired
-
1903
- 1903-11-12 DE DE1903165561D patent/DE165561C/de not_active Expired
- 1903-11-14 DE DE1903165562D patent/DE165562C/de not_active Expired - Lifetime
-
1904
- 1904-01-28 DE DE1904170657D patent/DE170657C/de not_active Expired - Lifetime
- 1904-01-28 DE DE1904170555D patent/DE170555C/de not_active Expired - Lifetime
- 1904-11-08 FR FR349353A patent/FR349353A/fr not_active Expired
- 1904-11-08 FR FR4154A patent/FR4154E/fr not_active Expired
- 1904-11-08 FR FR4155A patent/FR4155E/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE752285C (de) * | 1942-04-29 | 1953-07-13 | Henning Laokoon Chem Pharm Wer | Verfahren zur Herstellung von 1, 3-Dimethyl-4-imino-2, 6-dioxohexahydropyrimidin |
| DE1130812B (de) * | 1960-06-24 | 1962-06-07 | Dresden Arzneimittel | Verfahren zur Herstellung von 4-Aminouracilderivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| DE170555C (en:Method) | |
| FR349353A (fr) | 1905-05-26 |
| FR4153E (fr) | 1905-06-05 |
| FR4154E (fr) | 1905-06-05 |
| DE170657C (en:Method) | |
| FR4155E (fr) | 1905-06-05 |
| DE165561C (en:Method) | 1905-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH493528A (de) | Verfahren zur Herstellung neuer substituierter Aminopyrimidine | |
| DE165562C (en:Method) | ||
| DE1059459B (de) | Verfahren zur Herstellung des therapeutisch wertvollen 3-Sulfanilamido-5-methylisoxazols | |
| DE1792708A1 (de) | Verfahren zur Herstellung von Bisimidazolinderivaten | |
| DE1250828B (de) | Verfahren zur Herstellung des spasmolytisch wirksamen 6,7,3',4' - Tetraäthoxy -l-benzyliden-1,2,3,4tetrahydroisochinolins und seiner Salze | |
| DE156901C (en:Method) | ||
| DE676049C (de) | Verfahren zur Darstellung von Monourethanen der Alkylendiamine | |
| DE756489C (de) | Verfahren zur Herstellung von C-Cycloheptenylbarbitursaeuren | |
| DE958197C (de) | Verfahren zur Herstellung von 2, 4-Diaminochinazolin | |
| DE1670143C3 (en:Method) | ||
| DE848043C (de) | Verfahren zur Herstellung von Formylverbindungen des 2,6-Dioxy-4,5-diaminopyrimidinsund seiner Methylderivate | |
| AT163204B (de) | Verfahren zur Darstellung von C-C-Cycloheptenylalkyl- oder -alkenyl-barbitursäuren und ihren Salzen | |
| AT338800B (de) | Verfahren zur herstellung von 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)-6-chlorpyrimidin | |
| DE956306C (de) | Verfahren zur Herstellung von neuen Derivaten des Pyrimidins | |
| DE828541C (de) | Verfahren zur Herstellung von Acylaminobenzolsulfonylguanidinen | |
| AT239797B (de) | Verfahren zur Herstellung des neuen 3-Phenoxypropylguanidins und seiner Säureadditionssalze | |
| DE875523C (de) | Verfahren zur Herstellung von am Stickstoff mono- oder asymmetrisch disubstituiertenPentamethylendiaminen | |
| DE537366C (de) | Verfahren zur Darstellung von C, C-Alkylaryl-N-methyl- oder -N-aethylbarbitursaeurenund ihren Salzen | |
| CH357400A (de) | Verfahren zur Herstellung von 2-Oxo-hexahydropyrimidinen | |
| DE1445469C (de) | 1 - Amino^-hydroxy^-phenyl-piperidinderivate, ihre Säureadditionssalze und Verfahren zu ihrer Herstellung | |
| DE156384C (en:Method) | ||
| AT346848B (de) | Verfahren zur herstellung von 2,4-diamino-5-(2- methyl-4,5-dimethoxybenzyl)-pyrimidin | |
| DE964495C (de) | Verfahren zur Herstellung eines neuen Thiosemicarbazids | |
| DE1085884B (de) | Verfahren zur Herstellung von Pyrimido[4, 5-d]pyrimidinen | |
| DE1124504B (de) | Verfahren zur Herstellung von 2-Methyl-3-(2',4'-dimethylphenyl)-4-oxo-3,4-dihydrochinazolin. |